6344-46-3

Upstream product

• 98-88-4 benzoyl chloride 
• 102518-21-8 methyl 2,3-di-O-benzoyl-β-D-glucopyranoside 
• 709-50-2 methyl beta-D-glucopyranoside 
• 117124-69-3 methyl 2,3-di-O-benzoyl-β-D-galactopyranoside 
• 1824-94-8 methyl beta-D-galactopyranoside 
• 51996-18-0 C₆H₇O(OCOC₆H₅)3(OSO₂CF₃)(OCH₃) 
• 124314-27-8 methyl 2,3,6-tri-O-benzoyl-4-O-(trifluoromethylsulfonyl)-β-D-galactopyranoside 
• 4137-35-3 methyl 2,3-di-O-benzoyl-α-D-glucopyranoside 
• 10364-94-0 1-benzoylimidazole 
• 97-30-3 methyl-alpha-D-glucopyranoside 
• 613-90-1 benzoyl cyanide 
• 7177-79-9 methyl 2,3-O-dibenzyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 6748-85-2 methyl 2,3-di-O-benzoyl-4,6-O-benzylidene-α-D-glucopyranoside 
• 3162-96-7 4,6-O-benzylidene-1-O-methyl-α-D-glucopyranoside 

Downstream Products

• 910887-17-1 methyl-[O²,O³,O⁶-tribenzoyl-O⁴-(toluene-4-sulfonyl)-β-D-glucopyranoside] 
• 908574-92-5 methyl-(O²,O³,O⁶-tribenzoyl-O⁴-methyl-β-D-glucopyranoside) 
• 185115-20-2 methyl-[O²,O³,O⁶-tribenzoyl-O⁴-(toluene-4-sulfonyl)-β-D-galactopyranoside] 
• 122204-35-7 methyl 4-O-(2,3,4,6-tetra-O-benzyl-α-D-glucopyranosyl)-β-D-galactopyranoside 
• 122204-36-8 methyl 4-O-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-β-D-galactopyranoside 
• 125177-49-3 methyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside 4-(2,3,4,6-tetra-O-benzyl-α-D-mannopyranosyl phosphate), triethylammonium salt 
• 131150-19-1 methyl 2,3,6-tri-O-benzoyl-β-D-galactopyranoside 4-(2,3,4,6-tetra-O-benzoyl-α-D-mannopyranosyl phosphate), triethylammonium salt 
• 122204-31-3 methyl 2,3,6-tri-O-benzoyl-4-O-(2,4,6-tri-O-benzyl-3-O-methyl-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 122204-33-5 methyl 2,3,6-tri-O-benzoyl-4-O-(2,3,6-tri-O-benzyl-4-deoxy-4-fluoro-α-D-galactopyranosyl)-β-D-galactopyranoside 
• 51385-57-0 methyl 4-deoxy-β-D-xylo-hexopyranoside 
• 19467-77-7 methyl 2,3,6-tri-O-benzoyl-4-O-(p-tolylsulfonyl)-α-D-glucopyranoside 
• 73703-00-1 methyl 4-O-methyl-α-D-glucopyranosiduronic acid 
• 81348-22-3 methyl 2,3,6-tri-O-benzoyl-4-O-benzyl-α-D-galactopyranoside 
• 74593-33-2 C₃₅H₃₂O₁₁S 

Relevant academic research and scientific papers

4-(tert -Butyldiphenylsilyloxy)-2,2-dimethylbutanoyl: An Easily Removable Pivaloyl-Type Protecting Group with High Orthogonality

Protecting groups play multiple and vital roles during the synthesis of carbohydrates and other natural products. We herein report the installation and orthogonal cleavage, under mild conditions, of a 4-(tert-butyldiphenylsilyloxy)-2,2-dimethylbutanoyl (BDMB) group as a sterically hindered pivaloyl-type hydroxy protecting group. The compatibility of this substituent with the removal of other protecting groups is also investigated. Due to its advantageous properties, BDMB is anticipated to function as a valuable agent for masking hydroxy groups.

COMPOSITION COMPRISING SULPHATED GALACTOSE, AND IMPLEMENTATIONS THEREOF

The present disclosure discloses a composition comprising: (a) at least one sulphated galactose; and (b) at least one saccharide selected from a group consisting of disaccharide, trisaccharide, tetrasaccharide, pentasaccharide, and salts thereof. The pres

Introducing Oxo-Phenylacetyl (OPAc) as a Protecting Group for Carbohydrates

A series of oxo-phenylacetyl (OPAc)-protected saccharides, with divergent base sensitivity profiles against benzoyl (Bz) and acetyl (Ac) were synthesized, and KHSO5/AcCl in methanol was identified as an easy, mild, selective, and efficient deprotecting reagent for their removal in the perspective of carbohydrate synthesis. Timely monitoring of AcCl reagent was supportive in both sequential and simultaneous deprotecting of OPAc, Bz, and Ac. The salient feature of our method is the orthogonal stability against different groups, its ease to generate different valuable acceptors using designed monosaccharides, and use of OPAc as a glycosyl donar.

Mapping the Relationship between Glycosyl Acceptor Reactivity and Glycosylation Stereoselectivity

The reactivity of both coupling partners—the glycosyl donor and acceptor—is decisive for the outcome of a glycosylation reaction, in terms of both yield and stereoselectivity. Where the reactivity of glycosyl donors is well understood and can be controlled through manipulation of the functional/protecting-group pattern, the reactivity of glycosyl acceptor alcohols is poorly understood. We here present an operationally simple system to gauge glycosyl acceptor reactivity, which employs two conformationally locked donors with stereoselectivity that critically depends on the reactivity of the nucleophile. A wide array of acceptors was screened and their structure–reactivity/stereoselectivity relationships established. By systematically varying the protecting groups, the reactivity of glycosyl acceptors can be adjusted to attain stereoselective cis-glucosylations.

Total synthesis method for xinaomycin

The invention belongs to the technical field of pharmaceutical chemistry and organic synthesis, and aims to provide a chemical total synthesis method for xinaomycin. The method comprises the steps of:using D-galactose and the like as raw materials, firstly carrying out 8 steps of reactions to obtain a compound 14, then performing condensation on the compound 14 and uracil to obtain a compound 15,performing 4 steps of reactions to obtain a compound 19, performing condensation on the compound 19 and a compound 6 to obtain a compound 20, and finally removing an ester protecting group and a Cbzprotecting group in turn, so as to obtain the natural product xinaomycin. The total synthesis method of the present invention is a method for synthesizing the natural product xinaomycin for the firsttime. The total synthesis method has the advantages of high product purity, low cost, simple operation and the like.

Deprotection of silyl ethers by using SO3H silica gel: Application to sugar, nucleoside, and alkaloid derivatives

We applied a desilylation procedure using SO3H silica gel, with the surface modified by alkylsulfonic acid groups, to silylated sugar, nucleoside, and alkaloid derivatives. The treatment with SO3H silica gel provided desilylated products in good to excellent yield. In the reactions of sugar and nucleoside derivatives, no silyl residue was detected in the crude products, but the crude products of the reaction of alkaloids contained small amounts of silyl residues. Even though the sugar and nucleoside derivatives had a labile glycosyl and C–N bond, respectively, these bonds tolerated the reaction conditions. These outcomes suggested that the desilylation procedure using SO3H silica gel would be applicable to the deprotection of a variety of types of compounds protected by silyl groups. In a gram scale experiment, the desilylation procedure successfully proceeded without the observation of any silyl residue in the crude product.

Stereoinversion of Stereocongested Carbocyclic Alcohols via Triflylation and Subsequent Treatment with Aqueous N,N-Dimethylformamide

A convenient method for the stereoinversion of secondary alcohols, applicable to stereocongested carbocyclic substrates, is reported. A simple three-step procedure, including triflylation of the hydroxy group, nucleophilic oxygenative displacement by the treatment with aqueous N,N-dimethylformamide (DMF), and methanolysis, allowed for efficient stereoinversion of various substrates, including sugar derivatives, in one pot.

Synthesis and binding affinity analysis of positional thiol analogs of mannopyranose for the elucidation of sulfur in different position

Synthetic routes towards thio-α/β-d-mannose derivatives are presented. Double parallel or double serial inversion was successfully applied in the efficient synthesis of 2-thio- or 2,4-di-thio-mannoside derivatives. The protein recognition properties of th

Glucose positions affect the phloem mobility of glucose-fipronil conjugates

In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.

Glucose positions affect the phloem mobility of glucose-fipronil conjugates

In our previous work, a glucose-fipronil (GTF) conjugate at the C-1 position was synthesized via click chemistry and a glucose moiety converted a non-phloem-mobile insecticide fipronil into a moderately phloem-mobile insecticide. In the present paper, fipronil was introduced into the C-2, C-3, C-4, and C-6 positions of glucose via click chemistry to obtain four new conjugates and to evaluate the effects of the different glucose isomers on phloem mobility. The phloem mobility of the four new synthetic conjugates and GTF was tested using the Ricinus seedling system. The results confirmed that conjugation of glucose at different positions has a significant influence on the phloem mobility of GTF conjugates.